Synthesis of Some Phenolic and Amino derivatives of Cinchoninic Acid

Treatment of cinchoninic acids (1a,b) with allyl bromide afforded compounds (2a,b), and the hydrolysis of (2a) gave the 2-(4`allyloxyphenyl) cinchoninic acid (4) . Glycedylation of compound (1a) afforded compound (3a), while glycedylation of compound (1b) gave compounds (3b) and (3bb). The acetylation of the acids (1a,b) gave the acetyl derivatives (5a,b) . Benzylation of the amino compound (1b) with m-fluorobenzyl chloride afforded compound (6) . The reaction of compounds (1a,b) with allyl isothiocyanate or amino compound with carbon disulfide afforded thiocarbamate (7a), thiourea (7b) and dithiocarbamic acid (8) which is used as a synthone to prepare allylic ester of dithiocarbamate (9) respectively . Finally Compound (1b) can be transformed to a glycene derivative of cinchoninic acid (10). The synthesized compounds were confirmed by the physical and spectral means in addition to the functional groups systematic identification . INTRODUCTION As a part of our continuing study of the derivative of cinchoninic acid, we have turned our attention to use atophan (2-phenyl cinchoninic acid) containing OH or NH2 groups attached to phenyl ring at para